A busy Monday features the completion of the third round in men’s singles, as well as all round of 16 matches in women’s singles.
Italian No.1 Jasmine Paolini will walk onto Campo Centrale early in the day on Monday, to face 2017 Roland Garros champion Jelena Ostapenko. She will be followed by another Italian No.1, as well as the World No.1, in Jannik Sinner. And to start off the night session on Campo Centrale, former Italian No.1 Matteo Berrettini plays recent Madrid champ Casper Ruud.
Monday’s schedule also includes plenty of other intriguing contests, and features five of the last six women to win the US Open: Naomi Osaka, Aryna Sabalenka, Bianca Andreescu, Coco Gauff, and Emma Raducanu, with Gauff and Raducanu facing off against each other.
Throughout the tournament, this preview will analyze the day’s two most prominent matches, while highlighting the other notable matches on the schedule. Monday’s play begins at 11:00am local time.
Jasmine Paolini (6) vs. Jelena Ostapenko (17) – Not Before 12:30pm on Campo Centrale
Paolini is following up on her breakout 2024 season with a pretty solid 2025. She’s 18-8 on the year, and a was a semifinalist in both Miami and Stuttgart. And she hasn’t dropped a set through two rounds at her home country’s biggest event. Jasmine recently split with Renzo Furlan, her coach of 10 years, and started working with Marc Lopez, the former doubles partner and longtime confidant of Rafael Nadal.
Ostapenko is just 13-10 this season, but she did win the title a few weeks ago in Stuttgart, where she defeated both Iga Swiatek and Aryna Sabalenka. Jelena also reached the final of Doha back in February, a run which also featured a pair of top five victories, including one over Paolini. Yet outside of those two weeks, she’s only won three matches in another very streaky season. Ostapenko only had to play one match to advance to this stage, as she received a walkover in the last round.
In addition to their meeting in Doha, Jelena also claimed their only other previous encounter, two years ago at the US Open. But in front of a partisan Italian crowd, and considering how unreliable Ostapenko has been this season, I like the more consistent play of Paolini to prevail on Monday.
Matteo Berrettini (29) vs. Casper Ruud (6) – Not Before 7:00pm on Campo Centrale
Ruud is now on a seven-match win streak, after collecting the biggest title of his career in Madrid. He won a three-setter in his Rome opening round over Alexander Bublik, bringing his 2025 record to 22-6. Casper is a three-time semifinalist on Rome, where he is now 14-5 lifetime.
Berrettini has unfortunately missed this tournament in all of the last three years, as his injury woes in recent seasons are well-documented. And he’s just 13-9 on the year, and had to retire two weeks ago in Madrid after reinjuring his abductor. Matteo appeared rather healthy though on Saturday, in his opening round victory over Jacob Fearnley.
Matteo holds a slight 4-3 edge in their head-to-head, but on clay, Casper leads 3-1. That includes a win in a third-set tiebreak at this very tournament back in 2020, though it’s worth nothing that was during COVID and without fans in the stands. However, Berrettini’s only clay court victory over Ruud came in Madrid, which historically plays much quicker than just about any other event on this surface. In the slower conditions of Rome, especially during the evening, Casper must be favored to even their head-to-head.
Other Notable Matches on Monday:
Peyton Stearns vs. Naomi Osaka – Osaka is now on an eight-match clay court winning streak at all levels, after claiming a Challenger title a week ago. Stearns upset Australian Open champ Madison Keys on Saturday in a third-set tiebreak. This is their first career meeting.
Jannik Sinner (1) vs. Jesper de Jong (LL) – Sinner returned to competition on Saturday night with a straight-set victory over Mariano Navone. De Jong is a lucky loser who had never even appeared in a Masters 1000 main draw prior to this fortnight, yet upset Alejandro Davidovich Fokina in the last round with the loss of only two games. At last year’s Australian Open, Sinner defeated de Jong 6-2, 6-2, 6-2.
Coco Gauff (4) vs. Emma Raducanu – At 2023’s Australian Open, Gauff defeated Raducanu in a tight two-setter, their only meeting to date. While Emma is just 11-8 on the year, Tennis Abstract reveals she’s taken three of her last five matches against top 10 players.
Elina Svitolina (16) vs. Danielle Collins (29) – Collins beat a struggling Iga Swiatek on Saturday. Svitolina won this title back in 2017 and 2018, though she hasn’t advanced beyond the quarterfinals since. Danielle leads their head-to-head 2-1, but all three of those matches took place on hard courts.
Clara Tauson (22) vs. Mirra Andreeva (7) – Andreeva owns two straight-set victories over Tauson from earlier this year, including in the final of the WTA 1000 event in Dubai.
Bianca Andreescu vs. Qinwen Zheng (8) – A recently-returned Andreescu has already take out both Donna Vekic and Elena Rybakina during this tournament. Three years ago in Bianca’s home country, Qinwen defeated her in a three-hour three-setter.
Aryna Sabalenka (1) vs. Marta Kostyuk – This is a rematch from just two weeks ago in Madrid, where Sabalenka defeated Kostyuk in two sets decided by tiebreaks, but the match was not without controversy. Sabalenka paused play for a considerable amount of time after missing a first serve, telling the umpire it was raining too hard to continue. The umpire eventually gave in and stopped play, with Kostyuk protesting how her opponent would get a first serve upon resumption, since Sabalenka had basically brought the match to a halt herself.
Monday’s full Order of Play is here.
